Greg Proops (2010): Proops, who grew up in San Carlos, frequently returns to San Francisco. He'll appear with Whose Live Anyway? at the Marines Memorial Theatre on Nov. 19, and is doing stand-up at The Punch Line from Dec. 28-31.

What started as a quick sound bite-filled conversation about SF Sketchfest has detoured down the Greg Proops rabbit hole. The comedian riffs humorously for nearly four minutes about KSFO radio hosts of the 1970s. Six minutes, 15 seconds covers the now-defunct Circle Star Theater.

Proops is halfway through an inventory of the various young drug suppliers working in San Mateo's Hillsdale Mall circa 1977 when he interrupts himself.

"How are you going to put any of this in the article?" Proops says. "This can't be of any interest to anyone except you and I."

That's the gift and the curse of Greg Proops. The San Carlos-raised comic, who honed his act during the San Francisco comedy boom in the 1980s, doesn't do one-liners. He's enjoyed a thriving career - traveling as a stand-up and starring in British and U.S. versions of "Whose Line Is It Anyway?"

But he's at his best leading a meandering, hilarious, biting, personal, nostalgia-heavy, politics-laced conversation. That describes his The Smartest Man in the World podcast, which Proops will record Feb. 2 as a Sketchfest event at the Punch Line.

"I've done so many things over the years, and I've never had more fun, frankly," Proops says of the podcast. "It's really the most rewarding thing artistically that I've ever done. I get to be myself and be sincere, like you and I are talking now."

Proops, who attends his fourth Sketchfest this year, appears in four more group-oriented festival events, including the Jan. 31 Comedy NightLife at the California Academy of Sciences. The Hollywood resident says he's been looking forward to Sketchfest.

"It's always something fun to do," Proops says. "The comics really hang around, and then afterward we all hang out together and drink. It's good fun."

Raised in San Carlos

Proops was born in Arizona but at a young age moved to San Carlos, living a block from his alma mater San Carlos High. (Former Michigan Gov. Jennifer Granholm was in his class of 1977.)

He went to College of San Mateo for a couple of years and attended San Francisco State, easing into the percolating comedy scene in the early 1980s. Proops was a regular in the clubs, including the Punch Line, where he now hosts an annual residency that culminates on New Year's Eve.

"I don't actually remember the first time playing (at the Punch Line)," Proops says. "But I opened, I middled, I headlined. I did the comedy competition there a bunch of times in the 1980s, which I never did very well in."

That segues to a very amusing tale of the time he fell asleep face-down on the Punch Line floor during Doug Ferrari's set, was woken abruptly, and took the stage with rug marks on one side of his face.

As recently as November, Will Durst told The Chronicle that Proops "might be the funniest man in America." But from the beginning, Proops was a "comic's comic," code for "probably not going to star in his own sitcom." He found possibly his greatest success appearing in the "Whose Line Is It Anyway?" improvisation show throughout the 1990s. An eclectic array of other gigs range from an appearance on "Midnight Caller" to half of the alien pod-racing broadcasting team in "Star Wars: The Phantom Menace," and four years as the voice of children's show contractor Bob the Builder.

Monster podcast

All of the above, and San Carlos stories, too, are fodder for the Smartest Man in the World podcast. It started in October 2010, with Proops talking about Jerry Brown and the American Civil Liberties Union, and has become a monster. The podcast is a loosely structured affair, usually a conversational performance in front of an audience, sometimes more than 90 minutes long. At a recent London recording, 275 people showed up.

Proops says he loves the concept of a one-on-one conversation with fans who may be in their cars, on a plane or in the kitchen.

"My wife said to me when we started it, 'This is the perfect thing for you. The perfect medium,' " Proops says. "And I said, 'It's so disappointing to find out after 30 years that the thing you're good at is sitting at a table and having a drink and talking.' "

Growing old gracefully is a common theme in Proops' comedy. He has a good story about the moment in the early 1990s when he decided to stop wearing skull shirts and leather jackets and switch to his current uniform of a suit and tie onstage.

"I've spent a lifetime on the stage doing improv and stand-up," Proops says. "Been on a million TV things. A million radio things. And now I can broadcast on my own sitting on a table with a newspaper in front of me. The audience is easy with it. I'm easy with it. It's enormously gratifying." {sbox}

Greg Proops records his The Smartest Man in the World podcast at 4 p.m. Feb. 2 at the Punch Line in San Francisco. For his other shows and the entire SF Sketchfest lineup, go to sfsketchfest.com.